All Things Must Pass
by HeySandyStrange
Summary: After his close encounter of the Gilmore kind, Dean contemplates and reflects on his life, past and present.
1. Chapter 1

Dean stepped out of the door and took a deep breath. Stars Hollow was pretty this time of year.

 _You made me feel safe…_

He slowly walked away from Doose's market, not bothering to turn around for another look-

 _I wish I met you when I was older…_

He shook his head. Weird, bumping into Rory. So different and yet much the same. She even had the same socially awkward way, except this time it seemed less endearing and more-desperate? Anxious? Her face had been pale and drawn, her eyes didn't seem quite as bright. Weird.

He almost walked by his parent's house, he was so lost in thought. But once the munchkins saw him, windows opened.

"Daddy! Jamie stole my Iron Man! I saw him with my own two eyes!"

"Oh please! That's a baby toy, I have my own!"

"Daddy, daddy, daddy-did you get me something?!"

He looked up at the second story window that used to be his room, where three little faces were crowded. He laughed and turned down the walk way to the house.

"I see you guys are better! I guess we can work on some homework now, so turn off the TV, turn off the x-box-"

He was cut off by collective gasps and the window shutting with a thud. He stepped into the foyer. He was greeted by his glowing, if tired, wife.

"Hey, babe. The boys treating you alright?"

"No worse than our soon to be bundle of joy," Jenny joked, her face breaking into that lovely grin of hers.

He patted the generous curve of her stomach.

"Tabby giving you crap again?"

Jenny snorted, leaning into him. She was small, barely coming up to his chest.

"Kicking, turning, punching, she's doing the works. I'm telling you, this is my last one. We've got a girl now, I'm telling you I'm-"

"-getting fixed," he finished for her. "Which I fully support, if that's what you want."

She looked up at him, fluttering her pretty brown eyes at him.

"Or _you_ can get snipped."

He laughed, spinning around until they were in the living room.

"Hey, I told you, I need to keep my options open. When you leave me, take the kids and all the stuff, I'm going to have find myself a sugar mama who has a ticking biological clock."

Jenny laughed and playfully punched him in the arm.

"You loser! I know you're just trying to dodge child support!"

"More like trying to find a way to pay for four kids if you wise up and leave me. My job with only pays so much. Hey, were is mom? Thought she'd be home by now."

"She went shopping a town over to pick up something special for dinner, since tonight is our last night. You know, she likes to spoil us like we are going crossing the country, not driving the three hours back to Pennsylvania."

He walked into the kitchen and opened the fridge, fishing out a bottle of Bud. It was close to dinner time, after all. Jenny watched him as he sipped it, envious.

"I can't wait to have my evening beer again! And my wine-coolers…did I ever tell you how much pregnancy blows?"

"Considering how you've been almost four out of the eight years we've been together, yeah, I know how much you hate pregnancy."

She sat down at the table, with that smile he knew too well. That flirty evil little smile.

"I can't help it if you have only gotten hotter. Stop being so damn sexy and agreeable. Better yet, stop knocking me up. You'd think my bloated, fat ass would be enough of a turn off."

He walked over to her and stood behind her. He bent down and kissed her neck.

" , I you will never not be beautiful to me, so you' outta' luck."

She laughed, a loud, gasping sound that was surprising coming out of such a petite, delicate-looking person.

"I'd say I'm pretty damn lucky, Mr. Forrester."

 _You made me feel safe-_

"Hmmpf."

"What's that, sweetie?"

"Oh, nothing. Did you ever just, I don't know, get confronted by the past?"

"Sometimes, why?"

He took another long drink of his beer.

"Nothing. It's nothing. I just got everything put into perspective."

* * *

Those years following High School, following Lindsay, following Rory had seemed to stretch on forever. Years of depression, hopelessness, dead end jobs and wasted potential.

Or so he thought at the time. Looking back, Dean had really only floundered for a few months, a year at best. The end of his marriage to Lindsay had been swifter and more uncomplicated then he had anticipated. Truthfully, at had been all too easy to sever ties with her. Sure, he'd loved Lindsay-loved how fun she had been, how ready to party, how she liked to talk and pal around. In the beginning she had been devoted, and seemed to want all the things he did. But after the wedding, it got _hard._ Suddenly Lindsay wasn't fun and friendly, but demanding and spoiled.

Still, it was almost sad how easily it had ended once all was said and done. Lindsay moved back home and their paths didn't cross much after that. He had been more upset about the fact there had been so little feelings to it. He'd remember what his dad, never one to mince words, had said to him about that.

" _You two weren't really in love, you were playing house! Its better it ended when it did, instead of ten years down the line when you had kids tying you together."_

Heh. Dear old Jimmy Forrester, preferred fiddling with radios, TV's and VCRs to talking but he could hit you in between the eyes with the truth. His namesake Jamie was already proving he could be as direct.

Then, of course, Rory. At one time he could've been marked as BR and AR, before and after Rory. She had been his first love, the one who got away, too pure, too smart, too—everything. She was the pinnacle, his hopes and dreams, the one no other woman could compare to.

Of course, he had been a _huge_ idiot. In more ways than one.

But, idiot though he had been, he did realize one day that he was stuck in a dead end of his own making. Truth was, Stars Hollow was great but it was never his home. It was Rory's, Lindsey's, Lorelai's, Luke's, and now even his parents' home. But, especially now, it wasn't his.

One night, he visited his parents after work. Another construction job, complete with minimum wage and a limited time frame. Then he'd be searching again.

He was sitting down with his dad in the living room, watching TV. His mom was talking with Clara on the porch. Dean and Jimmy had their usual comfortable silence, but he was feeling restless. He worked up the nerve to speak.

"So, uh, dad…I've been thinking that I need to make a change. I haven't been able to find a steady job and, honestly, Stars Hollow doesn't have that many opportunities. So, I was wondering…I've been thinking about the military…"

His dad, calmly immersed in show, snapped to attention. His eyes widened.

"Really, kid? I mean, I was thinking you might get fed up and go back to Chicago, but you're really talking the military? The Army, I hope?"

Jimmy had did a brief stint in the Army. It was just at the tail end of Vietnam, and he had been barely 18. He didn't talk about it much but he always expressed to Dean about the good being in the Army had done for him. That it had given him direction and skills.

Jimmy shifted his beer bottle between his hands.

"Kind of a big step, huh? And there still is a war going on, ya' know. Those are never fun."

Dean shrugged.

"I mean, I get it. But, school's kind of out of my reach right now."

"What about that one school you got into? The one a few hours from here?"

"That was almost 2 years ago. Besides, I only qualified for a partial scholarship and maybe a little financial aid. Unless I want to take out a loan and go into debt, I would be pretty hard. I want to travel a little too."

Jimmy chuckled.

"Travel you will, but not all of them are great places. Trust me."

"Yeah, well, it's just too much, dad. Being here."

His dad didn't have to ask. Other than some rampant gossip, the affair and end of his marriage to Lindsey, life had went on as usual. But less and less did Dean feel like he belonged here. Most of his friends come to him through Lindsey, who'd been very popular at SHH, so they went with her. His other friends had moved on to college or greener pastures far away from this stifling little town. Everyone else had a love affair with Rory Gilmore and he'd never felt quite as welcome after he'd helped "taint" her with the affair.

Jimmy cleared his throat.

"Amy and me, we've come to like this place a lot. Hell, I've been able to make a living because this town has never seen a small business it didn't like. But you've got things going for you, kid, you're too young to just settle. And anyway, you need to get a better damn job or you're going to end up in our basement. I'm not having that."

"Nether am I!" his mother called through the window, proving Clara and she had been ease-dropping the whole time.

"Tell you what, I'll help you research your options. Best thing is to pick a good MOS, one you will like and pick some skills up. Then we'll go down to the recruiter Monday. I still know I think or two about how the Army operates. We'll get you set up."

For the first time in a long time, Dean felt relief.

* * *

Author's note: This isn't my first attempt at a fanfic, but my first time actually going ahead and (gasp!) putting one up on the interwebs. If you can't tell, it is going to be Dean-centric, with minimal input from the Gilmore Girls or other main characters. Don't worry, though, I have a plan to have Dean interact with a surprising guest character.

Anyway, I always liked Dean and felt he got the short stick during the original run of GG. I was glad he was given a little redemption in the Revival and was extremely glad he seems to have absolutely no lingering feeling for Rory. I was going to keep this to a one or two shot but it might be a few shorter chapters. Basically, I'm just going to expand a little more on Dean's life as it was presented in the Revival, just to fill in some blanks that are bugging me. I'm trying to keep it in character insofar as I can, but am taking some liberties since Dean and his family member are such a blank slate. Anyway, let me know what you think


	2. All Things Now

All Things Now

"Aaron, you were hungry enough for pancakes but now you want to pick at you food?"

"But it's _not_ pancakes, daddy!"

"Mom, can I stay up later tonight? I want to spend time with Granny and PopPop before we leave tomorrow."

"So it has nothing to do with you trying to watch grown-up shows? I'm on to you, Mister…"

"Mom, did you really make pancakes for Aaron?"

"Let me spoil my grandbabies! I hardly see them."

"Jeez, Amy, they're here so often me and Dean'll need to start adding on to this house. And with the way these kids like to pop'em out-"

"Give me a break, Jimmy. Don't act like I didn't catch you looking at my Home&Design issue last week. You know, the one with the baby girl nursery spread?"

Dean looked around the dining room table at the chaos. His mom fussing and trying to accommodate everyone, or the kids at least, Jenny sitting between Jamie and Aaron as mediator and ground control, his dad carefully cutting up his food as if that was his only true focus. Little Grady, still under the weather but much better than he had been earlier that day, sat in his father's lap. Grady was quiet, even when he was healthy, but he didn't like to be left out. Dean loved his two rambunctious older boys but he felt a special protective bond with Grady. Clara joked that it was because the four year old had red hair like her and it was only natural, as he had always protected her.

Crazy though it was-crazy, stressful, tiring-Dean loved this big family he had helped create. Most of his friends, the one's from high school, the one's from his single days, couldn't believe how he'd thrown himself into fatherhood and marriage with such gusto. He had been only 25 when Jamie had been born. But a wife and, better yet, a friend like Jenny and a bunch of children was what he'd always wanted.

After corralling and cajoling the boys into getting ready for bed, Jenny and Dean finally had some time to relax. They sat on the porch with his mother, enjoying the cool dusk. Jimmy claimed he had some work to finish, something to watch on TV. They all knew he was sneaking the boys' cookies and ice cream.

Amy sipped her beer and sighed.

"Ever think of moving back, sweetie? Star's Hollow my not have much, but it is a good place to raise kids."

Dean gathered Jenny into his side on the porch swing. Jenny and her belly settled into him, resting her head against his shoulder.

"Naw, mom. I've got too good a job, we have good friends, and the kids' have friends and school. I just don't think we would make out as well here."

"Plus, I'm not sure I how'd I feel about living in a town that has no less than three stores that sell cat figurines," Jenny added, shaking her head.

Amy had to laugh at that.

"Well, its five stores now, but you don't have to be such a glamorous snob, Jennifer Savatier Forrester. Not all of us are so well traveled."

"Well, Amy O'Sullivan Forrester, an Army Brat is the best kind of brat, what can I say."

The two women laughed together.

"Well, I have to say, I have nothing to be ashamed of when it comes to my kids. At least you both knew how to go out into the world and not come crawling back. Did I tell you about the over 30 club?"

"The who what?"

"The over 30 club. Or maybe it is the 30 something gang, I forget. Some of them are probably kids you went to school with. There are six or ten of them. They all came running home and are living off their parents, for the most part. And you'll never believe who one of them is."

Dean knew right away.

"Rory, right?"

His mom was surprised. She dropped her head to one side and gave him her patent x-ray eyes.

"I saw her at the store. She seemed…different, but then again I haven't seen her in forever."

"Well, apparently she has no real job and is living back at her mom's. Pretty shocking when you consider where she graduated from and the kind of money her grandparents supposedly have."

Jenny shrugged. She knew of Rory, even met her once very briefly but didn't have the preconceived notions about her the Amy had, rightly or wrongly, picked up.

"It's rough out there. I'm just lucky I got into nursing, there are usually always jobs in that. When Tabby is school age I'm going to get back in. But what was Rory-a writer? No, a journalist, right? That has got to be a hard field."

"Still, considering she was the "Great White Hope" of this town it is still crazy how _that_ turned out."

Dean shrugged. His wife was feeling heavier and heavier on him.

"Babe, go to bed. You're about to pass out on me."

"You're strong," she murmured. "You can carry me."

"Yeah, but not young like I was. I threw out my back the other week when I tried to lift Aaron up."

"That one is really going to get the tall Forrester genes," his mother predicted.

When Jenny was finally off to bed herself, Dean remembered that he promised someone he'd stop by before he left town. He let his wife and mom know, took two beers out of the fridge, and left out the front door.

* * *

It was as easy as a handshake, a lecture, and a test. As promised all those years ago, Jimmy had went with Dean to the nearest Army recruiting office. They had talked to a surprisingly friendly young man that went by Sgt. Thomasson. He was set up to complete the official ASVAB test and see what his options were for a career.

At first Dean had figured he'd get into something mechanical, maybe repairing Humvees. Instead, he ended up in communications, like his father had. Though, as Jimmy liked to say, he's son had totally one upped him by becoming Satellite repair man.

Looking back, Dean had to laugh at how naïve he was about the whole process. Sgt. Thomasson had assured him that if he physically fit, did as he was told, and "got a damn haircut," he would do just swell. Oh, would he.

He really had though himself a man, or at least a grown-up, but the Army proved to him just how young he really was. The grueling weeks of Basic Training, the long, intense months of learning his profession- _that_ had kicked him hard in the ass. But he made it, through it all despite some close calls, and he'd never felt prouder of himself.

Having made it through, he found himself plunked down in the exotic locale know as Fort Meade, Maryland. Not exactly the adrenaline pumping action hub of the military, but he liked his job, had friends, and adjusted well to Army life.

His first two years in the Army were the closest experience he would have to college life. In other words, he worked hard during the week and partied harder on the weekend. Hard for himself, anyway. Dean didn't lose his head, but he had his fair share of hangovers, three one night stands, and late nights clocked in at clubs. As one friend put it, "Rich kids go to college to have fun, and we go to the military!"

It wasn't really him, but he was glad he had that time to just be young and single, without responsibility. That had been his problem before with Lindsay, thinking he was some kind of adult who was ready to settle down when he was really a kid who needed to figure shit out. Lucky he did, because it got him ready for when Jennifer Rose Savatier waltzed into his life.

More like danced. He first saw her at a club, late one Saturday night. He had walked to the bar to get some refills for his friends. He wasn't feeling the drinking, the music, the whole scene. Truth be told, he was growing a little weary of the life of a single soldier and was starting to think a good old-fashioned relationship again. That's when he saw her, dancing under the pulsing lights-

Honestly, he noticed the redhead that towered over Jenny. He didn't have a type, to be exact, but he did like a taller women. Jenny's friend Kayla fit that bill. He went back to his table and gathered some courage.

"Go over and try to dance with her!"

"Get her a drink, first. Her friend, too."

"Come on, Forrester! Do it, do it!"

Dean always thought looking for a relationship in a seedy club was the definition of pointless, but he decided to at least try to strike up a conversation. He walked over, thinking to wait until she left the dance floor to try to talk to her. Like most things in life, it didn't go as planned. All he remembered was seeing a drunken guy trying to pawn on Kayla and a small whirlwind hit the guy, in the form of one Jennifer Rose Savatier. She had grabbed her friend and delivered a kick to the guy's groin.

"She said she wasn't interested! Take a hint, dumbass!"

"You little bitch! Nobody was talking to-"

Dean walked behind the guy and grabbed him by the collar.

"You need to leave before you say anything else. I take by the haircut you are from Meade; get a ride back to the base before I have to call your command."

They guy muttered but went back to his group. Jenny had looked up at him, her dark eyes shining with admiration.

"Thanks! Wow, some dudes, right? Can I get you a drink?"

He had nursed a beer for a better part of the night, talking to Jenny. Kayla had joined them in the beginning, but she excused herself from their table with a wink after a little while. They talked about everything and nothing. Jenny told him about her love for soccer and how she played all during school, how she was in her last semester of nursing school and wanted to work with kids or old people. She even got into the joys and downfalls of being the child of two career Military parents, including having changed schools at least seven times in her life.

She certainly was different from the two other girls that had captured Dean's heart in the past. She wasn't gentle, quiet, or intellectual like Rory or a girly,social butterfly like Lindsay. But he found himself very interested in this no-nonsense, down-to earth girl. It had been awhile since he felt like he had connected with someone like this. Someone he could talk to, whom he understood and who seemed to understand him.

"Well, Jennifer—"

"Call me Jenny! We've only been talking like, how long?"

"It is almost four thirty in the AM, so you tell me."

"Oh wow! Luckily I don't have school or work tomorrow."

"Me neither, or I'd be in serious trouble. Sooo, Jenny—what do you think about doing this again? I mean, not in this lovely place, some place nice."

She had grinned and tilted her head, as if she couldn't quit figure him out.

"I guess Kayla wins that five bucks, then. Damn it, I planned buying some trash bags with that."

"Uh, what now? Did I miss something?"

"We noticed you, noticing one of us. I thought you were eyeing Kayla and wanted to dance with her, and she said she bet you going to ask me to marry you or at least ask me out on another date. Since she put in the date part, I have to give her five bucks. I'm poor, if you can't tell."

He got a good chuckle out of that.

"Glad I could amuse you guys. So, about that date? Also, you said you like camping to, right? My friend Ramirez and his wife invited me on the next four day weekend, and I'm sure they won't mind if you came along…"

Exactly one year and two days later, when he married the very beautiful and radiant Jenny, he made sure to thank Kayla for winning the bet.

* * *

This place never changed. Star's Hollow was still the perfect little snow globe town it had been when he first moved here, all those years ago. He walked through the town center, smiling and waving along the way. Ms. Patti was still at it, leaning out of the open door of the dance studio to give him a long, lingering look as he passed, telling him that "fatherhood agrees with you, darling." For some unknown reason, Kirk had a pig now (Dean guessed cat Kirk finally bailed on him) and was always walking around town with him. Babette and Morey were pulling there once kitten now elderly cat Apricot along for an evening stroll.

He had a special destination in mind. A small house in one of the small neighborhoods in town. The person he was looking for wasn't hard to find, being that he was sitting on the porch.

"Hey guy," Dean said as he walked up. "Did the family relegate you to the porch for the duration of you stay?"

Jess snorted and rolled his eyes over his lowered book.

"Trust me, I relegated myself. Have a seat in this fine establishment and give me a beer, I need one."

* * *

Thanks to everyone who read and reviewed the first chapter! I finally got around to finishing up this chapter. Hopefully it is okay, I felt like it got long and too wordy in places. I'm terrible at self-editing, I'm afraid:) There should be one more chapter to this, which I will try to get out soon since I have some free time now.


	3. All Things Gone

All Things Gone

Dean handed Jess a beer and took a seat in a worn rocker. Jess popped the top and took a long gulp.

"Wow, pace yourself," Dean joked.

Jess snorted and wiped his mouth.

"Family, what can I say, Deano? They can't all be the Waltons like yours is. My mom and TJ are…mom and TJ."

"Your only here because Lorelai and Luke are getting married, right? Congrats to them."

"What, you weren't invited? I think the whole town is coming tomorrow. Even Taylor and Kirk are invited."

"Yeah, well, Jenny and me have to get the kids back home. School, you know. Besides, I'm not family or a friend, really, so it'd be kind of…weird."

"I think Lorelai still wishes Rory had snagged you up when she had the chance. Especially when she sees you with your wife and your kids."

Dean shook his head.

"I don't know—"

The door opened then. A young girl in pjs poked her head out. Even in the dark Dean noticed how sharp her dark eyes were.

"Hey, are you going to read to me? I want to hear a few more of Miss Zelda's poems."

"I'll be up in a few, kiddo. I left a bookmark in that one book, _Number the Stars_. You can work on that."

She gave a dramatic sigh.

"All right. Don't be too long, I have to sleep 'cause of the wedding tomorrow."

After she left Dean said, "Dina is growing up. Got the reading thing from you, huh?"

"Doula, actually—"

"Ouch," Dean said with wince.

"No freaking kidding. She is _smart._ Between my mom and TJ, I don't know how they did it. Well, they are pretty good parents when they aren't involved with vegetable cults."

"You'll have to tell me about that one when we have more time to bs."

"Tell you about it? Hell, I'm going to work it into my next novel."

"Oh, I finally finished your last one. For a biting satire of the millennial generation, I enjoyed it even if I wanted to punch every other character."

"Really? My message was achieved. Jackpot. I have reached, nay, _influenced_ my twenty fans."

Dean gestured with his beer can to the book in Jess's hands.

"Did Zelda finally put out some more poems? I'm not much of a poetry fan but I like her style."

"Well, when your literary influences are Toni Morrison, Shel Silverstein and Rumi, you somehow get one Zelda Shay-James."

"Not that I know her like _you_ do, but I think Ms. Shay-James is an original."

"You aren't wrong there."

They stopped talking for a few minutes, just enjoying the night. Then Jess shifted in his chair and turned to look Dean full on.

"She wants a kid. Wants a family, the whole package. She wants it to be me, if I'm willing. But she doesn't want to wait much longer. She's not pressuring me, but I know what she wants."

Dean guessed what Jess was looking for. He was the neighborhood old married guy, after all.

"I'll admit, I didn't peg you for the settling type, and definitely not Zelda."

"Not marriage, mind you, not right away, but a stable, semi-permanent relationship between two adults. As crazy as it sounds, I'm really agreeable to it."

"I guess the most important thing is, are you guys on the same page with what you want? Are you compatible? Do you…love each other? As more then friends with benefits?"

"Yes," Jess said without a second thought. "On the compatible and love part."

"Then what's stopping you? Is it…wait, is it Rory?"

Jess's shot him dire look. He must have hit a nerve there. Jess got the snarly look of old, the patented don't screw with me glare.

"Please. I hardly know her anymore. Crap, we dated more than a decade ago for less than a year, and it ended badly. I'm not even thinking about that."

Dean laughed. He put down his empty beer can.

"If you want my advice, here's how you know you've meet the right person and let go of the past…"

* * *

As easy as 1, 2, 3. That's what they always said, though they probably didn't mean three kids hurdling into the world in rapid precession.

Jenny was pregnant with Jamie less than two months after they got married. Not three months after the birth of their oldest they were shocked to find out that they were expecting Aaron. Shocked but not dismayed, as Dean and Jenny had agreed that they wanted two or three children that were preferably close together in age.

Adjusting to married life and parenthood was hard enough, but there was other dynamic shifts going on in Dean's life at the same time. A few months after he proposed to Jenny he was mulling over what to do as the end of his time in the Army approached. He had distinguished himself as a hard-worker who knew how to take an order and had the potential to be a leader. It was suggested to him that if he re-upped, he'd be on the fast track to get his sergeant rank and go on to bigger and better Army things.

Overall, Dean liked Army life, the sense of security and camaraderie that it afforded. But he was still unsure. He did miss the more laid back pace of being a civilian, of having more control over his life and putting down roots instead of the constant movement. He had talked it all over with Jenny.

"You know, honey," she'd said over dinner in her little apartment. "I want you to be happy. I know the life of dependent, so I can deal with it. Hell, I could teach you a thing or two. But…if you want me to be honest, I'd think I'd prefer raising our family as civilians."

Dean was surprised. Jenny was the only child of two Army sergeants, First and Master SSgts. Savatiar. She was close to her parents and very proud of them and the fact she had been an Army Brat.

"Don't give me that look," she muttered, eating the spaghetti Dean had made for her. "You're a great cook, by the by. When I told my mom you were a good cook, she told me I had chosen well."

"The perks of being a bachelor who likes a good home-cooked meal. So, back to what you were saying."

"Oh! Honestly, I love my parents and I loved growing up in the Army family, but it isn't an easy life at all. Plus it would be nice to put down roots, so our kids can grow up in one place."

He understood that. Not that he let it show much, but the move to Star's Hollow from Chicago had been an odd experience for him. Going from a huge, gritty city to small town America had been a bigger adjustment then he'd let on at the time. Maybe that was one of the reasons he first noticed Rory, someone who looked as alone as he had felt.

"Okay then, I guess I better start building up my resume."

He put in for as many jobs as he could in the months leading up to his exit from the Army. On top of his training in satellite maintenance and repair, he had gotten a CCNA certification in networking. He also had a decent amount of college credits under his belt. His dad had advised him to use his time wisely while he was single and in the military. Dean was very glad he'd listened to him.

He'd gotten some promising leads but was surprised when he landed an interview for a satellite repair at the Tobyhanna Army Depot in Pennsylvania. A logistics center for the military, it was where most of the computer and surveillance systems where repaired and maintained. It was an entry level position with good benefits and a decent starting salary.

"Tell you command you need some time off," his father-in-law Bob had advised. "You're clearing out anyway. That would be a hell of a good job for you."

He didn't go into it with many expectations, but low and behold, he managed to get the job. So Jenny and him set down roots in nearby Scranton.

Some guys at work joked that he was whipped, since he didn't have much time to hang out or have a beer after work. With Jenny working the weekend shift he took care of the kids. Even when they made the mutual decision that it would be easier for her to stay at home after Grady was born, he found himself running errands after work to take some of the load off Jenny. Yeah, sometimes it would be nice to hang with the guys and blow off some steam, but he also didn't want to miss being with his family every minute he could. So it was picking socks up from the craziest of places, giving three squealing boys piggy back rides, and watching crime show reruns with Jenny before they went to sleep. Even with all the bullshit, life had a way of working itself out.

Life also had a way of coming back around, he found. His tentative friendship with Jess was a good example of that.

Grady was almost two when Dean got the opportunity through work of attending some extra training in Philadelphia. It would be a week long and Dean hesitated to go. Jenny assured him she had it handled, that it would be good for his career and it might help him get another promotion.

In-between classes one day Dean wandered into a book store. Or at least he had thought it was only a bookstore. He got lost in the books, artwork, and the eclectic people milling around. He was checking out some science-fiction when he noticed someone come up wheeling a dolly of books.

He looked up. Jess stared back at him.

"Huh," Jess said.

"Yup," was all Dean could say.

They seized each other up. Jess hadn't changed too much, just gotten a little older like he had. He seemed cautious but maybe more relaxed than he had been before. Jess gestured to the book in Dean's hands.

"Didn't know you were into sci-fi. Or that you liked to read."

"Oh this? I wasn't but believe it or not, my mother in law got when into some of the harder science fiction. I used to read when I was younger but kind of fell out of the habit until recently."

Dean stuck out his hand.

"Sorry, how are you? I haven't seen you since before graduation. Do you work here?"

Jess was a little thrown off but he took his hand and shook it.

"Yeah, work here, help run the place, got a stake in it. You take your pick."

"Oh wow, that's pretty cool. This is one of the more interesting book stores I've seen in a while."

Jess started stocking the shelves.

"Yeah, we are also an independent publisher and printer. So you've always like to read? What's your poison?"

"Generally American writers, Steinbeck, Brautigan. Thomas Wolfe is one of my favorites. I've gotten into Robert Heinlein recently. Oh…Phillip K. Dick. Loved _Do Androids Dream of Electric Sheep_?"

Jess looked at him.

"Wow, I didn't know that about you. I mean, not that we hung out in high school or anything."

"You were too busy being emo in a corner and macking on my girlfriend."

A little bit of the old, temperamental Jess came out then with a narrowing of his eyes. Dean threw up his hands and laughed.

"Just kidding man! It was a long time ago. I'm not holding high school grudges, I'm a happily married man."

Jess relaxed again and even grinned a little.

"Sorry, I took some offense to the emo thing. So, why did I never see you read back in the day? All I remember is you playing every sport, going to church with your family and dating the blonde, Lacey or Lindsay. Did you end up staying with her, by the way?"

"Naw, it imploded between us. Lindsay and I were a bad match. She's a hair stylist in North Carolina now. I'm married to someone else. Anyway, yeah—I used to read a fair bit when I was younger. I don't know, outside of Rory no one at Star's Hollow High was into reading for fun. I got busy with my job, sports, school work and reading for the hell of it dropped by the wayside."

When Jess was done shelving books he paused for a second.

"We have a little coffee shop, more like stand, in here if you'd like a cup. My treat."

"I'm game. Coffee shop, huh?"

"Well, we had a bar for a while that I _thought_ was legal, until I found out my partner never bothered to get the licenses required to operate a fully stocked bar."

"Okay, how did you get out of that?"

"Let's just say, dumping a bar full of expensive liquors down the toilet at 2 am on a Saturday night is more taxing then you'd think."

They ended up talking for almost an hour, and Dean came back at lunch everyday while his class lasted. After that, they would meet sporadically over the next couple of years, whenever Dean and family were in Philly, when Jess happened to pass by Scranton, or those rare times both were in Star's Hollow. They weren't exactly bffs, but they had an easy understanding when they were together.

Life was really strange sometimes.

* * *

"…So that's how I knew she was the one for me. I asked her to marry me that night."

Jess snorted.

"Kicking a guy in the balls was what turned the tide for you?"

"Nope, the coincidence was what got me. Same guy she kicked the first night I meet her, he was drunk, though this time it was at a barbeque. And she would've walked away but the asshole remembered her and wanted to pick a fight. It was almost exactly a year to the day that I meet her. I pulled out the ring right then and there and asked her."

Jess shook his head.

"A romance for the ages."

Dean looked up at the sky. It was late, the stars were shinning bright. He needed to get home soon since they were leaving early tomorrow. But he felt there was something more he needed to tell Jess.

"Romance? It's not really about that, when you get down to it. I chased the fantasy enough to know that it never pans out in the end. I can't even say it was love at first sight with us. But I got to know Jenny, we had a lot in common, we both wanted a family. It's real. It's not always fun, but we've got each other's backs and we've worked hard for the life we wanted together. If Zelda and you are on the same wavelength and are willing to work through all of life's bullshit, you two have a pretty good chance of making it work and finding some happiness."

Jess didn't respond right away. He considered things very carefully.

"If I'm honest," he said, "I'm kind of afraid. I don't understand this family crap very well. I didn't have a real, happy couple to learn from growing up. I've only had two relationships with women that meant anything, first Rory and now Zelda. I screwed up with Rory and I've been on the verge with Zelda more than once."

Dean stood up.

"The only thing I can really tell you, man, is that you can't live in the past."

"Get that off a cereal box?"

"I wish. I had to screw up and fall on my ass a few times to learn that."

Dean started down the front steps.

"Just do what feels right. And compromise. Learn to compromise."

"Will do. I'll be seeing you."

"If you end up marrying Zelda or having a commitment ceremony or whatever you artistic, free-spirits do, let me know. We'll get you guys a present."

"Forget present, you both are invited. Bring the whole litter, I need some more hands on experience if I want to try this parenthood thing that is all the rage."

Dean was at the sidewalk but turned around.

"Hey Jess?"

"Yes?"

"There is more to life then Star's Hollow, ya'know?"

"Trust me, I know."

But what they were really saying, Dean knew, was there was more to life than a certain Gilmore girl.

* * *

 **Author's Note:** Well this got long. I liked the idea of Jess and Dean meeting up as grown-ups and actually finding some common ground. I actually think Jess and season 1 Dean had some things in common—both moved to SH from big cities, both seemed well read and worldly. I never was happy with how I felt Dean was dumbed down in later seasons, so I tried to give some logic to his changes. I never liked teenage Jess but I've grown to like the adult version to the point that I think he is waaaaay to good for present-day Rory and I'd prefer to see him with someone else, thus I have him contemplating taking the plunge Zelda. In the frame of my story Jess was only making eyes at Rory through that window because he is on the verge of making a decision about his future with another woman and was feeling some nostalgia in regards to his past relationship with Rory. That's my story and I'm sticking to it, lol, even if it barely makes sense.

Anyway, I'll be adding a short epilogue to tie things up. Hope you all enjoy, thanks for reading!


	4. All Things Pass

All Things Pass

"Jamie! Help me out here!"

It was barely seven A.M. and Dean's hands were loaded down with suitcases, blankets, and toys that missed being packed. He was putting everything in to the back of their SUV as Jamie rolled out of the house.

"I have the x-box and the video games," he said, proud of himself.

"The most important things, huh? Grady, don't drag your blanket on the ground."

Grady wrapped his blanket around his shoulders like a cape.

" 'Kay, daddy. Look, Aaron, I'm Superman!"

"Whatever, Batman is better. And Iron Man the best!"

"No they aren't!"

"Yes they are!"

"No-"

"Batman and Iron Man are both great," Jamie reasoned, "But I think Luke Cage is waaaay cooler."

"That's all great, kiddos, we all love superhe—wait, Luke Cage? Have you been watching Netflix behind our backs again, Jamie?"

Before his oldest could protest his innocence, Jenny appeared on the front step. She was pulling a large suitcase.

"Wait, baby, I'll get that!"

Jimmy walked out behind her and grabbed the suitcase from her hand.

"Got it, son."

Jenny rolled her eyes, folding her arms over her stomach.

"Jeez, I'm not an invalid. I'll remind everyone that I was jogging up until my five month with every pregnancy."

Amy also walked out on the porch and put an arm around her daughter-in-law's back.

"Which is why you get that cute figure of yours back so fast. Let us spoil you, Jenny, you do so much for my knuckle-head son and those gorgeous boys."

Jenny rolled her eyes at Dean as his mom led her to the car, though it was all in good fun.

It seemed to take forever but the finally had the car packed and everyone settled in. His parents promised to visit them soon, just in time for Jenny to have Tabitha in two months. His parents confirmed one last time that Clara would be home in time for the birth of her first niece. They waved them out at the end of the driveway, until Dean had lost sight of them.

"Wow, the gazebo is pretty! Are we missing one of those crazy awesome festivals this town loves so much?"

"I heard someone is getting married, so yeah, we are missing one of this town's crazy awesome festivals."

Out of the corner of his eyes, Dean saw two solitary figures in the gazebo. Both had dark hair and fair skin, so far has he could tell. He imagined they both had amazing blue eyes.

He remembered a time when he'd kill to have those amazing blue eyes look at him, that pretty mouth smile at him. But it was gone again in a flash.

He glanced at his wife's soft brown eyes, her long hair dancing in the breeze of the open window. He looked back at the three boys behind him, laughing at some shared joke.

He smiled at Jenny.

"I'll just be happy to be home, baby."

Author's Note: Well, here's the end of this little fic. Thanks to everyone who read it, reviewed, favorited and followed it. I know Dean is a hard sell, so it really means a lot that people enjoyed this fic. I've been tossing around some fic ideas in my head to build off of this one, maybe a one-shot of the births of Dean and Jenny's kids or something about Jess and my oc Zelda. I have a few ideas but have to see if I have the time.


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